And each 'bad' always brings to it a horrible UI change. Vista brought the window manager and those weird transparent windows and was generally ugly and buggy. Win 7 cleaned up the UI and made it flatter and simpler.
8 brought a full-screen start menu (!!). 10 went back to a 7-esque vibe (mostly).
11 is where we are.
2000->XP, forced online activation, if you moved from ME->XP they finally broke a lot of dos era apps. That isn't to say that XP is that far from 2000 which IMHO remains the best windows MS ever released (particularly after SP3). The only significant thing of value MS has added since XP, is 64-bit support, and that is questionable if you consider there was a 64-bit XP.
vista->7, this one is harder, maybe the biggest ding is, that this is where they started to remove all the classic mode UI paradigms that were in place for 15+ years. So, while vista was such a mess that going from XP->7 was a shock, even on a PC 2x+ faster the UI still lags because much of the win32 graphics stack and sound system is now emulated on the processor rather than handed off to the graphics card driver.
Win8->win 10, even more ad's, forced updates, can't permanently disable the virus scanner that eats 50%+ of the disk IOP rate, the list here is endless.
In the case of 10-11, I don't think anyone would really have cared if they hadn't decided to screw with the start menu/task bar again. That is the one thing that raises the ire of windows users, yet they seem to always screw with it. I think secure boot/etc is less of an issue for people than it was 15 years ago (and IIRC someone already has a workaround).
Vista tried a lot of new stuff, most of it was meh, then 7 came along and reined it in a lot, then we got 8/8.1, again, changing a ton of stuff unnecessarily in the name of updates, then 10 tried to strike a middle ground. Now we have 11, with its exceedingly aggressive hardware requirements and forced changes. With 12 we'll probably be back to MS trying to compromise so people move on from 10.
I think MS's issue with OS planning is that they really don't understand "don't fix it if it isn't broken", after every successful Windows version they get overly ambitious, change too much and push users away. Then for the following release they have to consider the fact that a large portion of their userbase hasn't upgraded, so they actually pay attention to feedback and try to compromise between what people want and what MS wants.